IP Library Granted Patent US 6,984,737
Granted Patent B2
US 6,984,737 · App. 10/181,744 · Granted Jan 10, 2006

Di(het)arylaminothiophene derivatives

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Quick Facts
Patent No.
US 6,984,737
App. No.
10/181,744
Granted
Jan 10, 2006
Kind
B2
Abstract

The invention relates to novel 2-(N,N-di(het)arylamino)-thiophene derivatives of formula (I), wherein R 1 , R 2 , R 3 , R 4 and R 5 are, independently each of other, each a monofunctional (het)aryl system and wherein R 1 can also be a bifunctional (het)arylene system, R 3 can also be a group R 8 , except when R 1 is a bifunctional (het)arylene system, R 8 representing chemical bond or a bifunctional (het)arylene system, R 4 can also mean R 10 , R 10 representing a chemical bond or a bifunctional (het)arylene system, or R 4 can be one of the following groups (II) and (III), R 9 representing a chemical bond or a bifunctional (het)arylene system and R 5 can also be H or (IV).

Claims (30)

1. A 2-(N,N-di(het)arylamino) thiophene derivative of the structure

wherein:

R 1 , R 2 , R 3 , R 4 and R 5 —independently of one another—are each a monofunctional (het)aryl system, in the form of a conjugated carbocyclic or heterocyclic ring system which may also comprise identical or different ring types which are linked or fused on linearly or at angles, it being possible for the peripheral hydrogen atoms to be substituted by alkyl, alkoxy, phenoxy, dialkylamino or diphenylamino groups (alkyl=C 1 to C 6 );

R 1 may furthermore be a corresponding bifunctional (het)aryl system,

R 3 may furthermore be a group R 8 , except if R 1 is a bifunctional (het)arylene system, R 8 representing a chemical bond or a bifunctional (het)arylene system;

R 4 may furthermore denote R 10 , R 10 representing a chemical bond or a bifunctional (het)arylene system, or R 4 may be one of the following groups:

R 9 representing a chemical bond or a bifunctional (het)arylene system;

R 5 may also be H or

the following may furthermore be the case:

R 4 and R 5 together form one of the following groups:

R 4 and R 1 together form the following group:

R 4 and R 3 together form the following group:

R 5 and R 1 together form the following group:

R 5 and R 3 together form the following group:

R 5 , R 4 and R 1 together form one of the following groups:

R 5 , R 4 and R 3 together form the following group:

Y in each case denoting CH or N.

2. The thiophene derivative as claimed in claim 1 , of the following structure:

3. The thiophene derivative as claimed in claim 1 , of the following structure:

4. The thiophene derivative as claimed in claim 1 , of the following structure:

5. The thiophene derivative as claimed in claim 1 , of the following structure:

Z denoting an anion and n denoting an integer from 2 to 100.

6. A process for the preparation of a thiophene derivatives as claimed in claim 1 , characterized by the following steps:

(a) reaction of a secondary amine with an acyl halide to give a carboxamide;

(b) conversion of the carboxamide into a thiocarboxamide;

(c) reaction of the thiocarboxamide with an α-haloacyl compound to give a 2-(N,N-di(het)arylamino) thiophene deriviative.

7. The process as claimed in claim 6 , characterized in that the thiophene derivative is converted oxidatively into a dimer or polymer.

8. The process as claimed in claim 6 , characterized in that the thiophene derivative is converted by means of an orthoformic ester or nitrous acid into a polythiophene derivative.

9. An organic light-emitting diode comprising a thiophene derivative of claim 1 .

10. An organic photovoltaic component or cell comprising a thiophene derivative of claim 1 .

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 2, 2015
From: OSRAM OPTO SEMICONDUCTORS GMBH
To: OSRAM OLED GMBH
Reel/Frame 036527/0179 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 28, 2005
From: SIEMENS AG
To: OSRAM OPTO SEMICONDUCTORS GMBH
Reel/Frame 017143/0859 →